Harem from the Future
by The Ruff Pusher
Summary: They claim to come from the future, and that all they want is him. How can Issei say no to these mature, sexy ladies? mature/harem/smut


**Note: This story is a work of fiction. It has many content of adult nature. If you do not want to read such content, please close your browser window or press the convenient back button.**

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"Issei?" He froze. A couple of knocks on the door accompanied Asia's question. "Are you there?"

Issei waited in heated silence like a statue, afraid that even moving one muscle would make some form of noise. He relaxed when he heard the sound of Asia's departing footsteps, though that didn't mean he was _completely_ relaxed.

His penis, for example, was still painfully erect, and was still being lovingly serviced by a trio of lovely ladies: which included Rias Gremory, Akeno Himejima-and Asia Argento.

How were there two of Asia, one might then ask? Well, one need not look far from the difference in their faces, to be sure. The Asia currently nibbling beneath his ballsack looked quite older, almost like one imagines a holy woman spreading faith and charity throughout the world; and yet in secret was actually a slovenly, perverted woman who enjoyed preying on younger men-which was exactly what this Asia Argento was doing, along with all the rest of the other women in this room.

While Issei had really wished for a harem, he hadn't known that it would lead to _this_ kind of situation. After all, one generally did not expect a literal orgy of one's friends' future selves, all looking much sultrier and more voluptuous and mature than their present bodies, all united in their purpose of pleasing him. It was exactly the kind of situation any man would dream of, and yet all Issei could feel (along with mind-numbing pleasure) was confusion. Why was this sort of Heaven happening, and what was he supposed to say to the future him?

Still, when their triple threat of tongue-licking action made his spine shiver six ways to Sunday, all such thoughts fled Issei's mind.

Older Rias was at the head of (giving) head, her much fuller lips wrapped tightly around his glans, her tongue swirling about the opening as if to coax the first few shots of his semen directly from his shaft. Her long red hair was shorter for some reason, though she kept her formidable hot and sexy figure.

An arguable second-place was Akeno-busy licking her way up and down one side of his veiny length-whose assets had literally ripened: in particular, her impressive fruit bags became even fuller, though with a slight droop now. Together, the three of them worshiped his tongue like some obscene phallic god, each lap of their tongue soaking more and more of his cock in their salacious spit.

And those three were not the only ones that had appeared. There, too, was Rossweisse and Xenovia, two beautiful ladies made even better with age, like vintage wine. In the case of the immortal valkyrie, her eyes had taken on the look of a mature seductress instead of the unsure virgin he knew her as most. And Xenovia's body had literally become something created by God specifically to breed, with love handles one could easily spend hours holding on to as one pounded into her with tireless speed.

Both of them flanked Issei as he stood: Rossweisse took his mouth, dominating him with such slimy techniques that sent pleasant shivers down his spine, while Xenovia cuddled and played at his other side, tweaking his nipples and placing small, ticklish kisses all over his sensitive torso.

It was as a gangbang, in reverse. No, one could more clearly see it as a harem situation gone wonderfully right, a fantasy becoming reality. And this didn't event feel like someone's tricks. He had a feeling something as lewd as this would have been outed as fake or fabricated if it had been a prank.

The combined sensations inevitably made him jerk backward, his back arcing as his orgasm shot free from his balls, his manly seed shooting out and coating the ladies below him in thick, white ropes. The trio sat back and basked in his shower, while Rossweisse and Xenovia made sure to steady him and his pulsing cock, pointing it towards the three kneeling ladies to make sure his cumshots struck gold every time.

When his intense orgasm ended, he was set down on the floor gently, positioned just enough to be able to see the impressively hot and lewd aftercare that occurred immediately after. Rossweisse and Xenovia joined the mass of flesh writhing on the floor, their bodies thereby getting tainted with his fresh cum. All of them wrestled with one another, jockeying for ultimate control with accompanying grunts, squeals and moans as they desperately sought to lap up all his cum from each other's bodies. For a while, Xenovia topped them all, taking advantage of the various headlocks and leglocks to freely lap up every string of cum from every girls' skin, until Rias broke free with a yell and slammed her against the floor, whereupon the other four proceeded to gang up on the poor girl, their tongues now racing over her body, the once-pure Asia even drawing her into a slutty kiss to fish out the cum still in Xenovia's mouth.

It was hard to tell who'd won or lost in the end, or by what means they'd declared their winner. But the contest did end, and all the ladies' attention went back to him. Aside from being very much aroused, there was also the instinctual fear, like he were facing a pack of monstrous beings whose only goal was to mate with him.

"Hey, Issei-kun, there're some things you need to know..." Rias said. She straddled him personally, her moist, hairy nethers rubbing lewdly against his hardening cock.

"W-what is it? You're Rias, right? Rias Gremory?"

"Of course," she replied, putting her arms to the side and wiggling her body such that her breasts jiggled right in front of his face. "Is there any doubt? Now, here is one thing you must know, Issei-kun.

"As you might have guessed, we did time travel from the future. That means we are definitely the future versions of the people you love at the present. It also means this event has been hard-locked in time."

"Hard-locked?"

"It is now happening, it will have happened, and will always happen. You're a virgin, aren't you?"

Issei blanched, his member even drooping slightly, as if it too had been insulted. "Y-yeah, so what?"

"Ufufu... I don't mean it in a bad way. It's just that..." She shared a look with the other women, who each had secret smiles of their own. "You lose your virginity today, at this very moment. Then, you will go on, using your newly found skills to devour each and every one of 'us', teaching us new and exciting ways to be lewd and depraved. And then... one day, in the future, knowing full well what will happen, _you_ will send us here, to this time, fully aware of what will happen at this point in time. Are you getting me?"

Issei's eyes widened. "Oh crap."

They all giggled. Of course. With their travelling here, it would always be a fact that Issei lost his virginity to "them". It also meant that, technically, in the far future, he would be cuckolded by-himself.

"NTR? Oh man!" Despite his sorrowful shout, his member seemed to lengthen, as if it were fully aware of the implications, and was eager to proceed already. _But no, it cannot be!_ This was so twisted! But it also sounded kinda good! Not to mention hot as fuck! An unknown sensation crept up through his spine, the anticipation of doing something so fresh and forbidden. And he was still even a virgin, damn it!

"And that means, Issei-san," said the gentle Asia, whose counterpart was in this very building. " _You_ will cuckold and be cuckolded by _you_."

"Be sure to remember well, Issei," said Rossweisse brightly. "Engrave this scene of debauchery in your mind, so when 'that' day comes, you will remember it as if it were just today."

"You will tell us stories of this day," Xenovia said dreamily. "Ahhh, to be bred by a man destined to be stolen from in his turn! You are indeed an interesting specimen, my husband!"

"Stealing and stolen, eternally entwined," said Akeno. "It's got a nice ring to it."

"Well then, now that that's settled," Rias said, her smirk widening. She laid her warm and soft hands on his chest, while softly rubbing her vulva against the side of his cock, slowly teasing her entrance with his glans. "Girls? Please remember this message, my dear. I'm sure it will provide an adequate 'side dish' for you as you wait back there."

They all cleared their throats, then they bent their heads forward, each of their faces side by side as their stares bore into him. They then recited, with practiced ease and in practical unison, the words: "Issei, I'm sorry. Another man fucked me. Another man stole me. Another man held their hot, stinking, sweaty bodies against mine, writhing endlessly against me, his cock stealing through my insides like they were his own. Yes, Issei, I lost to that man's cock. That man's name-is Hyoudou Issei."

Issei gasped mightily, their words seared into his head as his cock sank into the pleasant, slippery depths of Rias Gremory. A match made a long time ago, this woman whom he'd protected, fought for, and fell in love with-now he was sinking his cock into this woman. He slide easily inside her tight tunnel. When he was sheathed fully into him, Rias grunted, leaning against a supportive Akeno.

"Grk! You're definitely more impressive than my husband, _young man._ You're so thick and virile and strong... My husband can't ever match up to this cock." He didn't know why, but every word she said sent invisible daggers into his heart. It didn't help that he felt like he were in heaven, as if his cock were gripped in the vice of an organ designed to milk him for all he was worth.

"Congratulations, milady," Asia said. "You've stolen our husband's virginity."

"Congratulations, Issei," Rossweisse echoed, patting his forehead like he were a puppy.

"Thank you," Rias said graciously, right as she squeezed him tight and pulled her pussy up, then down his cock. The pattern repeated, again and again, gaining steam with every second. Every time his penis slid through her slimy depths he felt pleasure like he'd never felt before, certainly more than his lonely hand had ever produced.

Rias laughed, smooshing her boobs right in his face. "How is it, Issei-kun? How does it feel, my love? Your situation is one of the more unique ones I've ever heard of: not even the Fallen Angels could be this creative! How does this cheating pussy feel, Issei-kun? Does it feel great?"

"It's... gaaah... it's good! Fuck! Gah! Fuck! Riasss..." He apologized in his heart to his future self, but he would feel no guilt about it. His wife was smoking hot and he would enjoy being practically assaulted by this older, slutty woman! Mature woman banzai!

The room was slowly filled by rapid slurping sounds as her mature pussy glomped and squelched his cock greedily. By the time things started to get really wet and messy in their crotches, he was aware of other things happening in the background. Rossweisse had snagged a position behind him, his head practically in her lap pillow, "mothering" him with coos and headpats as he lost his virginity. She also leaned down periodically to claim his lips, her breath carrying a whiff of ripe fruit-raw and tantalizing. The two others passed the time double-teaming Asia, who whined piteously as Akeno and Xenovia dug in deep into her pussy. Wet shlicking sounds from her pussy echoed throughout the room, loud enough that Issei thought Asia's counterpart would come knocking again.

"Issei-kun."

"W-wha?" He blinked, and saw that Rias' head was in front of him again.

"There's just one last thing," she said, with an impish grin. "It's a secret: another thing you'll consider in the far future." Her inner folds squeezed against him, making him suck in his breath sharply. "All of us here... well, it's not our safe day."

"HOLY shit!" Issei practically shot up from Rossweisse' lap, his cock suddenly a lot harder and more vigorous in its thrusts. The wet _slap-slap_ of their union reached a fevered rhythm, as Issei pounded upwards harder. Rias squealed pleasantly, squeezing her pussy around his aching cock as she rode him with ever more ferocity towards his impending orgasm.

"Wait! Wait! Does that mean!" He looked around wildly, at the others whose expression was almost similar to Rias': like a cat that had well and truly swallowed the canary.

"One by one," said Asia.

"We'll all be fucked," Akeno said, tonguing the former holy woman's nipple.

"We'll all be bred," Xenovia corrected, her eyes shining.

"And you'll seed us, and give us children," Rossweisse whispered, like she were sharing some forbidden secret. She leaned down, offering a nipple for him to suckle hesitantly.

"All of it, behind our husband's back," Rias concluded, her supple pale skin rippling as her flushed skin rippled and bloomed with every bounce on his cock. "We'll come back to him-to _you_ -with another man's child seeded in our bellies."

"Remember this, Issei," they all repeated at once. Issei could not help it: the knowledge that one was going to procreate seemed to be ingrained in men to make them a thousand times more desperate to cum. Issei was already there at the threshold, and when the thought came to him of impregnating all these women, especially with the 'cheating wife' aspect, he could not hold back. For a brief, tortuous second, his upward thrusts ceased, his body going still as his balls churned up a second dose of white baby juice. Then in the next second, his teeth bit into the valkyrie's nip, making her hiss; his pleasure mounting like a volcano as he'd thrust his cock into Rias as far as he could. He felt his glans rubbing against a barricade of sorts, though he didn't care for anything anymore as his glans exploded with his restrained ecstasy, his seed painting the room of his future child with absolute, slimy white.

Rias came, or so it felt: his cock seemed like it was being gripped in something hard and painful, and yet all it made his cock do was pump up even more and more of his hot, virile semen, pushing it straight into Rias' womb with relentless speed and ferocity. Rias' eyes were closed, her arms crossed about her abdomen like she were trying to protect it, her devil's wings had appeared, and they quivered along with her body.

Her eyes opened, and they met Issei's. She smiled fondly, as the last bits of his orgasmic spurts died down. "Thanks, Issei," she said, as normal as Rias would have said it. She yelped, drawing her arms closer around herself as she was rocked by the aftershocks of her orgasm. "...Now I feel so blessed, to have conceived a child from another man's seed. You've made me so happy..."

"Congratulations, you two-husband, mistress," said a gushing Akeno.

"Uwaaah... Rias looks different. She's definitely on her way to motherhood, Issei," said Asia.

Xenovia rubbed his arm, and pinched it. "Please breed me as thoroughly as the mistress."

Rossweisse made a small, clapping sound, like she were a teacher making the class behaved. "Now now, we're all going to have our unfaithful wombs filled with Issei's seed today. No need to be so impatient. We've already got a queue system going, Xenovia. Next up is Asia." She cupped his face and gave him a quick peck on the lips. "Please give her a son our _husband_ never could, Issei."

Though he'd just came, Issei, or rather his member, couldn't say no to that. The older Asia waited for him on a futon they laid out on the floor. It seemed the others were in a way respectful of each other's limits and wants: Asia slipped under the covers, beckoning for him to go in with her, while the rest sat back and drank some tea that had been prepared-in the nude.

"I'm sorry for this," Asia said, her tongue gliding over his cheek. "I'm just so terribly shy."

"Oh. Haha... It's no trouble." He stammered. His body hung over hers, and he was unsure how to proceed. She nuzzled her thighs against his hanging "Oh! Or rather... um... I should be the one thanking you... Asia."

Asia paused, smiled, then gave him a soft, chaste kiss; while her soft, delicate hands ushered his cock into the steaming cunt readied for his entrance.

The others carried on a conversation which he did not really hear, as immersed as he was in this blonde beauty in front of him. Her insides, her lovemaking, this missionary position: everything about Asia was markedly different from Rias. But it was hard to term it "vanilla", because there was definitely nothing cute and pure about the way she'd immediately wrapped her legs around him, locking him in place; nor the way her pussy felt like a velvet glove that seemed to fit his penis perfectly, nor on the way she cried out "Harder! Fuck! Harder!" in a decidedly hoarse and slutty voice, like a bitch in heat, her every motion urging his thrusts ever deeper. Still, despite all that, she would always be the girl he'd sworn to protect. As he thought that, his second peak cumshot came crashing, bathing his mind in white.

When he came to, he heard someone sniffling. He looked and realized it was this Asia.

"What's wrong?" he asked, panicking.

"No, nothing, it's just..." Asia wiped away her tears, then glanced at the other women. "It's just as perfect... and wonderful... as 'our' first time."

Someone chuckled, the others sighed or made cooing sounds. Looking at the tearstricken Asia, Issei felt his cock harden. She noticed, smiling, though she pulled him out of her gently.

"I would love to," she whispered. "But we had an order to things. Remember this moment, Issei, and we shall come back to it when the time comes." Hard to believe he'd have to wait so long to get to _this_ Asia. He was almost taken aback by the thought: he already had his own Asia!

"It's my turn," Akeno announced, pulling him from his reverie, and out of the futon. The woman's eyes blazed with lust, something he had not seen in his previous lovers. Akeno crushed him to her breasts, sticking her tongue right in his mouth. A pleasant thrill went down his spine from their deep kiss, and he wondered if she had used her spells. Except it wasn't-the feeling was something else entirely. And that made his member poke hard against her navel, which made the busty woman chuckle.

"In my past, we invented plenty of games, you and I," she said. "Obviously, I can't share them with you now-it'd only spoil the experience for 'me'. What we are going to have, instead, is some wild, raw sex. So sit down, Issei. It's going to be a bumpy ride."

As he sat on a low table, Akeno indeed rode him hard. He spent much of their fiery lovemaking sandwiched between her impressive twin mounds. It almost felt like its own separate world, closed off from the rest. Small jolts of pleasure shot up from his cock buried in her folds, as if she had indeed cast her signature spells on it. As a result, his every thrust was like an endless dollop of thrills up his spine, producing a type of pleasure unique from the others. After a while their combined fluids began to mingle, and their skins shone with their mutual sweat saliva. As his hips began to rise up from the seat, his cock practically begging to unleash its second helping, Akeno leaned over and bit him hard on his shoulder.

"Ah~ That's unfair, Akeno!" someone said. The sudden feeling of pain, accompanied by the whirling dynamo of her inner depths, sent him over the edge. Her eager bouncing stopped, her thick and mature body slumping against his, as he pumped up his baby batter into her. He wanted to say she was heavy, though of course knew that was just the way to a bad ending.

"Can he still keep going?" Rossweisse asked, examining his moist cock after they'd pulled Akeno from him.

"Allow me." Rias leaned down and drew him into a deep kiss, while brushing her nipple against his shoulder. Immediately, his limp fellow rose to full. "There we go. He's all yours, valkyrie."

Rossweisse preferred to be ridden, and thus introduced Issei to something he'd only seen in pornos: doggy style. The older woman had perfectly-shaped round buttocks, so soft and squeezable, which one could easily lose one's hand. Issei mounted Rossweisse, using his past experience to find his own way through her wet and juicy entrance, and from there he let his instincts take over.

It induced him to pound the older valkyrie mercilessly. There were no kisses, no loving embraces, just pure, straight-up fucking, each of his desperate thrusts drawing a pronounced moaning sound from Rossweisse, like she were some sort of beast being rutted. Loud, smacking sounds came from the woman's pussy, and once more the sound of fierce lovemaking filled the room.

"Whoa, careful with that, lover boy, you'll break her hips," someone said. The others were having their tea in the nude, as before.

"I can attest to it," Asia said, grinning slightly. "My hips are as sore as the day 'he' took me."

All the women had their stained pussies practically displayed to him. His thick, drying semen pooled idly on the chairs of those he'd already creampied. Xenovia, who caught his eye, drew his gaze to her pink slit, which she spread in a lewd, inviting manner, her eyes doing a "come hither" impression.

"Shit!" Issei's passions multiplied, yet again, and he speared his meat through the valkyrie with even more speed and strength. All thoughts of other things other than sex sex sex were steadily erased from his mind. He was drawn into a dark, drunken frenzy from which pleasure was the only, ultimate release.

When he'd finished, Rossweisse was a sad sack of ruined, orgasming flesh, her womb well-seeded with him; while Issei rose, like a zombie, his cock still hard and wet with the fluids of four cunts, and fully ready to take a fifth.

The others moved out of his way as Xenovia waited on top of the futon with a seductive smirk, her legs wide open, her pussy practically offered to him like prized meat. And this beast named Issei took the bait, leaping on the woman, pinning her body under him and practically ramming his cock without foreplay into her needy hole.

"Yes! Yes!" Xenovia said, through gritted teeth, practically pumping his mouth with her hot, whorish breath as their tongues drew circles around each other. "Give me a child..! Give me the one you promised..! Ahn~! So long... ago! Issei!"

"Yes! Yes! Yes!" Issei obliged the bitch's words with the best his body could offer, his hard, well-oiled member rutting into the woman's hole like it were trying to dig into buried treasure. Their sweaty bodies moved in lustful unison, each move anticipating the next, in perfect tune, thrust against squeeze, sway against ram, tongue against tongue. There was no love but for the pleasure, no pleasure but one to be attained this very moment. Xenovia hissed against him, her insides heaving, rumbling around his cock as she came, her whole body slackening, defeated by his limitless passion. And yet he was not far behind-his victory leading way to the fulfillment of her deepest wish. In his dominance he was undone, and after however long years his cock erupted in thick, white ropes, coating Xenovia's womb with his strong male essence.

He stirred from the brief funk brought on by the orgasm-by the time he realized it, he was still on top of Xenovia, and his cock was still hard and ready inside her steaming cunt. He rose, his passions still seething, his lust still roaring in his ears. He turned his eyes to the other women.

"Oh my... Did you travel here as well, dear?" Rias said jokingly.

"It's too late, 'Issei'." Akeno said, pushing her hands into Rossweisse' and Asia's defiled pussies, and then licking their combined essences from her fingers. "We're already pregnant by another man. A better man."

"S-sorry Issei," said Asia. Rossweisse twiddled her thumbs, smiling at him bashfully.

It was as if past and future were united on this very moment: the he of today, devouring this wonderful women, and the he-who-would-be, destined to be cuckolded. The contradictory feelings merged, forming a limitless font of lust that would not be slaked until their bellies swelled from all the cum he'd pumped into them.

And thus, Issei charged back into battle, straight into history.

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 **Story is commissioned by The_Caroltine, thank you. Extra words on me, as usual.  
**

 **If you'd like a story commissioned, please contact me here, or on my tumblr, theruffpusherdottumblrdotcom.**


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